


Black Eyes and Black Leather

by TheLittleRedWhoCouldWrite



Series: Sam Winchester Reader-inserts [20]
Category: Supernatural
Genre: Cunnilingus, Dominant Reader, F/M, Light Bondage, Nipple Clamps, Orgasm Control, Submissive Sam Winchester, demon reader, unprotected sex
Language: English
Status: Completed
Published: 2017-10-17
Updated: 2017-10-17
Packaged: 2019-01-18 17:20:16
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,050
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12392589
Author URL: https://archiveofourown.org/users/TheLittleRedWhoCouldWrite/pseuds/TheLittleRedWhoCouldWrite
Summary: When Sam meets Cas’ demon friend, he works really hard to pretend his feelings don’t exist.





	Black Eyes and Black Leather

“Your source is late,” Dean grumbles, slouching in the diner booth next to Sam.

Cas rolls his eyes. “Y/N is usually late. If she’s less than fifteen minutes late-”

“- she’s early,” a female voice finishes.

Sam looks up to see an absolutely stunning woman standing by their table. Her grin as she slides into the bench beside Cas and presses a kiss to the angel’s cheek reminds Sam of Meg.

“Hiya, handsome,” she coos. “Sorry to keep you waiting. These your friends?” her eyes rake over the boys and Sam has the distinct feeling that she’s imagining him naked.

“This is Sam and Dean Winchester,” Cas tells her. “Guys, this is Y/N.”

Y/N’s grin gets wider. She leans across the table to shake their hands with her own perfectly manicured one. Sam wonders what she does that allows her to be able to help them out, but still keep her hands so soft and clean; or how much money she spends doing the latter.

“Winchesters,” she purrs. “I know all about you. You’re very important to Cas. He talks about you a lot. Especially,” she points at Dean, “you.”

“Do you have the info?” Dean asks, looking very done with this whole situation. “Or are we wasting our time?”

“Dean,” Cas scolds, glaring at him.

“Sorry about him,” Sam says, flashing Y/N a bright smile. He’s not sure he likes or trusts her yet, but Cas trusts her, and Sam needs to at least be civil.

“Oh, no, he’s right to question,” Y/N smirks. Her eyes flicker black a moment. Sam’s whole body goes rigid and he can feel Dean having a similar reaction beside him. “Smart man.” Her eyes return to normal. “But I assure you, I’m not here to do you harm. Meg introduced me to Cas a few years back. I’ve kept my distance, though. Didn’t want to bother you guys. You have quite the reputation following you around.”

Sam nods stiffly. “Do you have the information?”

“Of course.” She pulls an envelope from inside her jacket. “In here is everything I have on the demon known as Gremory. He’s not going to be easy to take down, but if anyone can do it, it’s you three.” She sets the envelope down and gives Cas a one-armed hug. “Call me when you’re done, Hot Wings. We need to finish our Lord of the Rings marathon.” She slips out of the booth, eyes lingering on Sam as she goes. “See you later, boys.”

Sam suppresses a shiver as she walks away, but he’s not sure if it’s disgust or arousal.

* * *

With Y/N’s info, the boys are able to bring Gremory down. Part of Sam doesn’t want to admit it, but he knows they couldn’t have done it otherwise.

After that first day, Y/N starts to show up regularly. Sliding into the booth beside one of the boys, randomly appearing in the back seat, knocking on the door of their motel room. Sam wants to not like seeing her so often- she is a demon, after all- but she’s smart and funny and definitely easy on the eyes. Even Dean admitted to that one. The more she’s around, the less angry at her Sam becomes.

He doesn’t want to feel things for this demon, though. Sure, she reminds him of Meg, but she reminds him of someone else, too. Especially with the rate at which she consumes french fries. It rubs him the wrong way. He lets it. It’s easier than admitting to the truth.

“Sam,” Cas says, sitting across from him in the bunker library- the one place Y/N hasn’t been yet. “Why do you hate Y/N so much?”

Sam glances up from his laptop. “What? I don’t hate her.”

“Well, you have a strange way of showing it. You’re never very nice to her. Even Dean seems to at least tolerate her presence, but you… she asked me last night what she could have done to upset you.” Cas leans his elbows on the table. “Sam, she’s a very dear friend. I would appreciate it if you tried a little harder. Get to know her. Maybe then you’ll see why I like her.”

“She’s a demon, Cas.”

“Well, I’m an angel. Dean was a demon once. You had demon blood in you. None of us have any room to cast judgement purely based on her species. That’s not fair to her.” Cas sighs, sitting back in his chair. “Please try to understand her? For me?”

Sam huffs softly, hunching over his laptop. “I’ll try.”

Cas lights up immediately. “Thank you, Sam. It means a lot to me.”

The thing is, Sam knows it does. He can see in their interactions alone how much Cas likes Y/N. Their relationship isn’t quite like the way Cas was with Meg- he always wondered if the two were in love. This is more like Sam and Dean. Y/N is important to Cas and therefore Sam needs to treat her better. He’s been kind of an asshole. There’s no other way to put it. She didn’t do anything to him, and definitely not anything to deserve to be treated the way he’s been treating her.

* * *

The next time they see her is at a bar after a hunt. She slips onto the barstool beside Sam, gesturing to the bartender for a beer like his own.

“Hey,” he says, trying to keep his tone light to disguise how he’s torn between disgust and arousal.

“Hey, yourself.”

“How have you been?”

She looks at him in shock. “You feeling okay?”

“Yeah, why?” he questions, leaning against the bar and turning his body towards hers.

“You’ve never once asked me that question,” she points out.

He shrugs. “I realized I was being kind of an asshole. Figured I should probably start acting nicer.”

“I thought ‘asshole’ was a Winchester character trait,” Y/N says, wrapping slim fingers around the neck of her beer bottle. Her nails are painted black today, but there’s a kind of glitter in them that shifts between every color of the rainbow, even in the dim lighting.

“Nah, it’s usually just Dean.”

That pulls a laugh from her, a soft sound that sends Sam’s heart racing. “Well,” she says. “I’ve been doing okay. Took down a vampire nest the other day.”

“You hunt?”

“Yeah, I do. I’m pretty sure I told you guys that.”

He ducks his head, a little sheepish. “I didn’t really pay attention. Sorry.”

“You were preoccupied with hating me.”

“I don’t hate you,” he insists.

She lifts an eyebrow at him. “Sure got a funny way of showing it.”

“Yeah, well, I’m trying to make up for that.”

“You’re doing okay so far. Cas told me about the hunt you boys just finished. You sure you should be drinking?”

“I’m fine. He fixed me up.”

“Huh.” She nods. “Perks of being friends with an angel.”

Said angel is across the bar, staring squinty-eyed at the pool table while Dean plays some local college kids out of their cash. Sam smiles fondly at the sight- Cas still sucks at poker, no matter how hard Dean works to teach him.

“I guess so,” he says. “But Cas is more than just an angel. He’s my best friend. One of the greatest guys I know.”

“He’s pretty awesome,” Y/N agrees, taking a long swig from her beer. “I like him.”

“I think he likes you, too,” Sam points out.

“I hope so, ‘cause he’s stuck with me.” She turns appraising eyes on Sam. “I think you’re stuck with me, too.”

“You think so?”

“Oh,” she grins, “I know so.”

* * *

Things get easier. Sam is able to find a sort-of in-between where he doesn’t have to admit that his feelings for Y/N are quickly growing, and doesn’t have to pretend to hate her. It’s nice. She’s fun to have around. She makes Cas laugh and drinks Dean under the table, and when she catches Sam staring, she just smirks knowingly and keeps her full lips pressed together. He appreciates her not saying anything; he’s not sure what he would do if she did.

The downside of admitting that he doesn’t hate Y/N is that it makes it harder for him to hide the fact that he really doesn’t hate her as time goes on. She seems to sense it. She sits a little closer, drops light touches across his shoulders when she walks behind him. Looks a little longer, a little harder, intense gazes that are definitely mentally stripping him of his clothes.

Sam can’t bring himself to mind.

* * *

“Morning, Sam,” Y/N says when he lets her into the motel room one morning before a hunt. “Cas said you guys might need a hand on this one. What’re we dealing with?”

“Looks like a witch,” Sam tells her, gratefully accepting the coffee she offers. “Might be a coven. Dean and Cas are at the morgue right now, but they should be back soon.”

“What do you guys have so far?” Y/N leans her hands against the edge of the table, studying the files Sam has laid out.

“Not much, unfortunately. Just a string of seemingly unrelated deaths by strange causes.”

“Classic witch style.” she nods. “If we find the connection between victims, we should be able to find the witch.”

“That’s the plan.” Sam returns to the chair he was occupying before Y/N arrived and pops open his laptop. “Wanna start going through the paper files while I dig into their online lives?”

“I’m down with that.” Y/N settles across from him and slides a file closer.

Sam’s not sure how long they’ve been sitting there when her foot rubs against his ankle. He startles a little, glancing up at her, and for a moment thinks he was imagining it, until it happens again. Her gaze flickers up to meet his and the corner of her mouth quirks upward. He bites the inside of his cheek to keep from reacting.

Dean and Cas choose that exact moment to return, saving Sam from humiliation.

* * *

With an extra set of eyes and hands on board, it only takes them a couple more days to find and kill the witch. Sam likes working with Y/N, he really does. She’s a badass huntress and Sam’s really glad she’s on their side. She would be a frightening opponent.

The thought weighs on his mind the same way it did with Meg and Ruby, back in their time, and he lets it slip from his mouth late one night after Cas has wandered off somewhere and Dean has passed out on the other motel bed. “Y/N… why are you on our side?”

“I never asked for this,” she replies, her beautiful, leather-wrapped curves draped across the couch, a half-empty beer bottle dangling from her fingertips.

He lifts an eyebrow in her direction. “That’s a new one.”

“Yeah, well, I didn’t actually sell my soul.”

Sam sits up straighter in his chair. “You didn’t? How’d you end up in hell?”

“There wasn’t a king to create order at the time, so demons weren’t following the rules at the time. Crowley had only just come to power as King of the Crossroads and hadn’t amassed the reputation he has now. Demons were snatching souls from reapers whenever they got the chance and, well, they snatched mine. Lasted a few decades or so on the rack before I gave in. Should’ve lasted longer.” She drinks deeply from her bottle.

“You lasted longer than a lot of people,” Sam tells her.

“Not long enough.”

He’s never heard her talk like this. If he hadn’t seen her drink Dean off the table and know she’s only halfway into her first bottle, he would think she was drunk. This is a whole new side of Y/N and Sam’s not sure how to react to it.

“Sorry,” she sighs, sitting up. “Didn’t mean to go all emo on you.”

“No, it’s fine,” Sam insists. “If you need to talk, I’m always happy to help.”

She gives him a tired smile. “Sam Winchester, you’re too good to me.”

Sam watches her down the rest of her beer and vanish into the bathroom. He’s not sure how much longer she’s going to stay, or where she’s going to go when she leaves. Ruby never slept, so he’s pretty sure Y/N doesn’t either.

When Y/N emerges from the bathroom, she looks better than when she went in. She starts gathering her stuff quietly, making sure not to disturb Dean as he goes.

“You don’t have to leave,” Sam says softly, dragging a finger through the ring of condensation his own bottle left on the motel table.

“No, you need to sleep,” she tells him. “I’ll see you in the morning.”

“Y/N,” Sam says, catching her attention just before she opens to door. She looks over her shoulder at him. “Thank you for trusting me.”

She smiles softly. “Thank you for listening.”

* * *

Y/N hangs around even more after that night. Sam doesn’t admit it, but he likes having her around. He can have in-depth, intelligent conversations with her that he can’t have with Dean- not because Dean’s not smart enough, Dean is brilliant, but because Dean’s not as interested in all the mythology behind the monsters they hunt as Sam is. He pouts and whines, but Y/N actively looks up new information to share when Sam the next time she comes around.

“So, you and Y/N seem to be getting along well,” Dean observes.

The three of them are in a bar after a successful hunt- Cas was called away on angel business and Y/N has gone to get more drinks. Sam can see her leaning against the bar, black leather jacket snug across her shoulders while she chats with the pretty bartender.

“Yeah, we are,” Sam agrees, shifting a little in his seat and trying his best to not look back toward Y/N.

“Sure there’s not more going on?” Dean inquires, nudging Sam teasingly.

Sam can’t help the blush that spreads across his cheeks. Dean lifts an eyebrow.

“Wait,” he gasps softly, “is there something?”

“I don’t know,” Sam admits. “I know how I feel, but I don’t know how she feels.”

“Sam, that’s a bad idea and you know it. She’s a demon.”

“You think I don’t know that, Dean? There’s a reason I tried not to get close to her at first, but I didn’t know how to do that without being mean to her and that wasn’t fair to her. She hasn’t done anything to us and even you like having her around.”

“Yeah, but not that much. She’s funny and nicer than Meg was, but I still don’t trust her.”

“Well, I do.”

“You do what?”

Sam hadn’t noticed Y/N crossing the room, and her voice as she slides a couple of beers across the table startles him. “Like audiobooks,” he spits out as quickly as he can think of it. “Dean thinks it’s dumb.”

“Audiobooks are great,” Y/N agrees. “I listen to them while I do my laundry and stuff. They’re great when you’re doing menial activities and want to get some reading done.”

“Exactly,” Sam agrees, glad his lie was believed.

Dean shakes his head, chuckling. “I’m surrounded by nerds.”

Y/N shrugs. “Perhaps. I don’t think you mind that much, though.”

Sam smiles, trying to keep the fondness out of his expression and hiding it behind his drink when he can’t. He uses his drink to hide his surprise, too, when a small booted foot nudges against his ankle under the table. His eyes flicker to Y/N’s face to find her watching him. The foot rubs along the curve of his calf, sending a shiver up his spine, and he knows she’s doing it on purpose.

Thankfully Dean is oblivious to Y/N playing footsie with Sam under the table and he’s able to keep his reactions to a minimum. She gives him a questioning look, but he doesn’t ask her to stop. Truthfully, he doesn’t want her to stop. Instead, he switches to water and stretches his leg out to hook his foot around her ankle. She relaxes with a smile and presses into the contact.

When Dean gets up to go to the bathroom, Y/N leans over.

“So,” she says slowly, resting her elbows on the table. “Wanna get out of here?”

That’s not what Sam was expecting to hear. “Like… right now?”

She sits back. Her foot falls away from his. “Sorry, I thought we were… sorry. I didn’t mean to… sorry.”

“No, I just… you caught me off guard,” he says. “I don’t usually… you know.”

“Sleep with women?” she asks. “Or demons?”

“… both?” he answers sheepishly. “I guess I’m just a little out of practice.”

“That’s okay,” Y/N says. “It takes two to tango, and I know how to lead.”

Shit, now he’s blushing again. He can’t remember the last time a woman made him feel like this- probably not since high school. He doesn’t see as many women as Dean, but he’s usually pretty confident with himself around them. Something about Y/N has him all him twisted up and he’s not quite sure how to handle it.

Sam bites his lip, staring at the mostly melted ice in his glass. He’s not sure how exactly he wants to handle this, but he does want it. He wants it bad. He tentatively stretches out his leg to nudge the toe of his boot against her calf. She looks up at him in surprise.

“I… would like that,” he says quietly.

Y/N grins. “Then let’s get out of here.”

Sam shoots Dean a text and leaves a few bills on the table, and follows Y/N out the door.

* * *

Y/N has a room in the same motel as the boys, but further down the row. Her small hand holds tight to Sam’s much larger one, clearly taking the lead. His stomach twists nervously while she unlocks the door and ushers him inside.

As soon as the door clicks shut behind him, Sam finds himself shoved up against it. He expects Y/N to kiss him, but she doesn’t. Instead she stares up at him with intense, questioning eyes.

“I need to know,” she says slowly, “that you will tell me if I go too far.”

“Like… like a safeword?” he asks.

“If that’s what you want.”

“The stoplight system. Red, yellow, green. Does that work?”

“That works. May I kiss you, Sam?”

He nods, biting his lip. She doesn’t move.

“Use your words, Sam.”

“Yes, please,” he gasps out, exhaling abruptly. He hadn’t realized he was holding his breath. “Please.”

Y/N curls a fist into his hair and yanks his head down. Their lips crash together hard enough to bruise. Sam whines, hands flying up to grab her hips and steady himself. There is no doubt as to who’s in charge here, and Sam knows that with anyone else he would be freaking out by this point. Something about the tight grip on his hair, the gentle hand running up his side over his shirt, the soft lips against his, tells him that he’s safe here. Y/N won’t hurt him.

“I want you naked on the bed,” she breathes, her words hot against his lips.

“Yes, ma’am,” he murmurs.

She grins wickedly and releases him. He quickly straightens up and starts stripping. He takes things slow, every movement purposeful in a teasing way. Y/N is stripping the comforter and blankets off the bed, but she still watches with hungry eyes as he unbuttons his shirt one by one. He drapes his shirt over the back of a chair and kicks off his shoes. He’s glad he did laundry recently and has clean boxers, because Y/N’s eyes go straight to his crotch when the dark red fabric comes into view. He’s already visibly aroused and the sight makes her grin.

“Someone’s excited,” she purrs, moving in to cup a hand around his bulge. His hips grind forward instinctively before he can stop them, but she just smiles wider and rubs along the line of his erection. “Lovely. So responsive. We’re going to have fun with that. Now, you have orders to complete.”

He nods and quickly strips off that remaining piece of clothing. His cock bobs up to smack against his stomach, rapidly growing to full size. Y/N stares openly and his cheeks heat up, but he forces himself to get up onto the bed. He stretches out on his back, hands by his sides, and holds still when Y/N comes to stand by the bed.

“Love this,” she murmurs, trailing a finger up the line of his stomach and smirking when his abs pull back from the tickling touch. “You’re gorgeous, Sam.”

His faces gets even hotter and he turns his head away, hiding a little in the pillow. He sees her frown out of the corner of her eye. The mattress shifts beneath him and suddenly she’s straddling his hips. He can feel the worn-soft fabric of her jeans against his cock, but his focus is on the hands turning his face to look her in the eye.

“I want you to look at me,” she says sternly. “I want to see your eyes. Understood?”

“Yes, ma’am,” he murmurs.

“Sam Winchester, you are beautiful,” Y/N tells him. “And you don’t get to cum tonight until you get that into your head.”

He’s edged himself before, but he has a feeling she’s going to take things to a whole new level. He reminds himself that he can back out of this any time he needs to.

Y/N presses down, rubbing her clothed crotch over his cock a moment before getting off him. His hips chase her for a moment before he gets control of them and she snickers.

“Are you gonna be still for me, sweetheart, or do I need to tie you down?” she inquires, hand still on his face.

The thought of being tied up by her has Sam’s dick jumping against his belly. He’s never been aroused by that before; he’s been tied up far too many times for that to ever be considered a turn on. But he wants to give her everything he has. He hasn’t wanted that since Jess.

“You want to be tied up?” Y/N giggles. “You like that idea?”

“Yes, ma’am.”

“Have you ever done that before?”

Sam shakes his head. “No… not like this.”

“Mmm. You’ve done the tying.”

“Yes, ma’am.”

“We’ll start with something simple.” Y/N crosses the room to her bags and pulls out several bunches of soft looking rope. “I’ll tie your wrists together, and then to the headboard. If you’re still okay after that, I’ll tie your ankles. Sound good?”

“Uh-huh.”

She sits by his head and takes one wrist in her hand. With the skill of someone who’s done this many times over, she ties his thick wrists together. The rope is tight enough to let him know it’s there and will probably leave some marks for him to run his fingers over tomorrow, but loose enough to let blood flow normally and remind him that he can get out of this if he chooses.

“How does that feel?” Y/N asks him, holding onto the loose ends of the rope so he can’t lift up his hands.

He tugs on the bonds, testing the give. The rope is gentle against his skin. “Good,” he tells her. “Feels good.”

“I’m gonna tie you to the headboard now.”

Sam nods and she secures the ends of the rope. When she sits up, he tests those knots as well and finds them to be pretty solid. She sets an end of rope in his hand.

“Pull this and the knot will come undone,” she says. “Ready for your ankles?”

He bites his lip, considering his predicament, and then nods. “Yes, ma’am.”

Y/N moves to the end of the bed, sliding her hand along one leg before settling on his ankle. Her thumb rubs soothing circles, the weight of her hand solid and reassuring. She loops the next rope around his ankle, being careful not to catch any hair in the knots. He appreciates the consideration.

When one leg is bound in place, Y/N pauses and sits up so she can see his face better. “Still good?” she asks.

“Green,” he says, nodding.

“Alright. Moving on to your other leg.”

She works with the same carefulness as before. When she’s finished, Sam finds himself completely immobile and strangely okay with it. In fact, he’s more than okay with it. Being completely at Y/N’s mercy has his cock dribbling a little clear puddle onto his abs.

“Ooh, someone is liking this,” she says, voice light and teasing as she climbs onto the bed between Sam’s spread legs. Her small hands run up his calves, over his knees, and settle on his thighs. “I like this, too, sweetheart. You look amazing, all spread out and hard and ready for me.”

Sam is blushing again, but he forces himself to keep looking at her. She didn’t tell him he could stop yet.

“Doing so good for me,” she assures him. “Are you ready to keep going?”

“Yes,” he breathes out, trying to tone down the desperation in his voice. “Please.” He adds in a hopeful voice, “Wanna see you.”

“You’re looking at me, darling. Be more specific.”

“Wanna… see you naked.” His words trail off in the end and she cocks her head.

“I’m sorry, I didn’t catch that.”

“Wanna see you naked,” he says with more conviction.

“There we go. It’s okay to ask for what you want, Sam, as long as you’re polite about it. I think you’re missing a word.” Her hands have moved up to his hips, fingers framing his cock without touching.

“Please,” he almost whines.

“Good boy.”

She sits up on her knees, shedding her leather jacket and then peeling off her shirt. Her bra is simple black lace and he clenches his fists, eager to touch. Her skin looks so soft and inviting and he wants to get his hands on it more than he wants to cum at this exact moment in time.

“Like what you see?” Y/N teases, stretching her arms above her head to show off.

He nods eagerly. She grins and quickly wiggles out of her jeans. Her panties match her bra and Sam knows she was hoping for this.

Y/N walks on her knees up the bed to straddle his face. Sam licks his lips, eyes locked on her face as he tips his chin up invitingly. She hovers her pantie-clothed pussy over his mouth, one hand coming down to rubs slow circles through the fabric. He can smell her arousal and it makes his mouth water.

“I want you to make me cum,” she orders, slipping her fingers under the elastic and pulling her panties to the side. Her pussy is soaked already and it looks amazing. “Go on. Do your best.”

Sam glances from her slick folds to her face and back. She’s hovering just out of reach and he realizes she wants him to work for it. He lifts his head and stretches, barely managing to run his tongue over the edge of her labia. He holds his head there as long as he can, fighting the pain in his neck in favor of serving his mistress.

Mistress.

He’s never thought of any woman like that before, but it fits here. It feels right in his mind and he’s sure it would feel right in his mouth.

“Want more?” she coos, rolling her hips a little lower. For half a second his tongue slips between her folds, but then she pulls back again. A whine escapes his throat before he can help it. “Patience, sweetheart.”

Sam lets his head fall back onto the pillow, biting his lip and gazing up at her with his best pleading eyes. She laughs and slides a hand into his hair.

“Get to work, sweetheart.”

That’s all the warning he gets before she lowers herself all the way down. He moans when the sweet taste of her hits his tongue, diving right in. She holds tight to his hair, riding his face with small movements of her hips. He takes his time to explore her, finding all the little spots that drive her crazy. She really likes it, for example, when he lets his teeth brush over her clit. It makes her body jerk and pulls a sharp sound from her lips. Armed with his new knowledge, he sets out to make her cum as many times as possible.

She’s beautiful when she cums. Her head falls back, her spine arches toward the ceiling. She braces herself with the hand in his hair and her free hand on his stomach. Her thighs tremble and clench around his head, and the sounds she makes. Helpless and uncontrolled grunts and sighs and wails that go straight to Sam’s dick.

“Fuck,” she gasps, rolling off of him before her legs give out entirely. “You’re good at that, baby boy.”

He grins. He’s still hard- so hard it hurts, really- but that doesn’t matter right now. All he cares about it that he brought Y/N pleasure and did a good job doing so.

“I wanna play with this now,” she purrs, scooting down to sit by his hip. One hand wraps around the base of his cock, standing it upright. “Such a pretty cock. Proportionate. This is going to feel so good inside me.”

Sam fights to keep his breathing steady when her other hand comes in to rub a flat palm over the sensitive head. She hums softly to herself, as if she’s not torturing the glans under the head of his cock with her thumb.

“Responsive,” she observes. “I think I’ll keep you, pet. How does that sound?”

“Please,” he manages. He wants her to stop, but he also never wants this to end.

“You wanna cum, don’t you.”

He nods frantically, curling his fingers around the ropes holding him down.

“Not yet. I decide when you get to cum.” with that, she lets go of his dick. It falls back against his belly with a smack that’s more arousing than anything else, to be quite honest. She traces a finger along the line of it. “Who’s cock is this, pet?”

Sam’s so focused on breathing that it takes him a second to process the question.

“Y-yours,” he stammers.

“Mine?”

“Uh-huh.”

She strokes a hand up his abs to his pecs, brushing her fingertips softly against his nipples. He inhales sharply and arches into the touch.

“Lovely,” she sighs. “We’re going to have fun with those. I want to try something. Tell me if you want me to stop.”

Before he can respond, Y/N leaves the bed and crosses the room to her bags again. This time she pulls out a thin chain with things Sam can’t quite make out on either end. She returns to his side and climbs up to straddle his hips, settling so her pussy traps his cock against his stomach.

“Color?” she asks, holding up the toy so he can finally get a good look at it.

Nipple clamps. She’s holding nipple clamps. Sam’s immediate instinct is to say no, but sight of them makes his cock twitch.

“Yellow,” he says.

She sets the clamps on his belly and leans down to kiss him softly. “Do you want me to find a different toy? Or just take this slow?”

“Slow,” he tells her.

“Alright. These clamps adjust, so I’ll put it on a lighter weight to start out and we can move to something heavier if you feel up to it. Does that sound good?” her face is inches from his, her eyes inquisitive and concerned.

“Yes, Mistress,” Sam murmurs, lost in her eyes.

She kisses him again, and then sits up. He watches her adjust the clamps before she plucks at one of his nipples. He gasps, but holds still for her. She makes sure his nipples are erect before carefully applying the clamps.

It hurts, but not like he expecting it do. This pain has his balls drawing up tight and his thighs trembling.

“How’s that?” Y/N asks, tugging lightly on the chain connecting the clamps.

“More,” he whines. “Please.”

She grins and complies, tightening the clamps. Sam almost wails, body arching off the bed and nearly dismounting the woman on top of him.

“Wow, you really like that,” she observes, running her fingers through the quickly growing puddle of precome just under his naval. His cock is still trapped by her weight. “You look amazing like this, Sam. So beautiful”

He shakes his head helplessly, pulling on the ropes holding him. “Not… no…”

“Yes,” she sighs, tugging on the chain again and smirking at his cry. “You are. I want you to repeat after me, pet.” She reaches down and pulls her panties aside again, the slick heat of her pussy finally coming into contact with his dick. She rocks her hips slowly. “I’m beautiful.”

Sam moans, but shakes his head again. It would be easy to say, but the words feel all wrong in his mouth. They can’t be true.

“Say it, Sam.” Y/N’s voice is sterner now, leaving little room for argument.

“I… I’m beautiful,” he whispers with a choked sob.

“Like you mean it.”

“I’m beautiful,” he says with a little more conviction.

A strangled cry is ripped from his throat when suddenly Y/N angles her hips just right and sinks down on his cock, all the way to the base.

“Cum for me, Sam,” she orders, pulling hard on the clamps.

The sound Sam makes is almost inhuman. His whole body tenses and trembles. His toes curl, digging into the sheets underneath him. His arms flex and the headboard creaks ominously, but holds. The pain in his chest just intensifies the pleasure pulsing through his balls and cock as he pumps Y/N full of his cum, just moments before his vision goes black.

* * *

When he comes to, Y/N is draped over his chest, watching him with a smug expression.

“Welcome back,” she says, carefully removing one of the clamps. He groans and she rubs the skin around his sore nipple, encouraging the blood flow back into it. “When was the last time you came that hard?”

“Never,” he answers. His voice is rough, worn. Maybe he was noisier than he thought. He feels a little bad for anyone staying in the neighboring rooms.

“Way to make a girl feel special.” The other clamp comes off, more soothing rubbing. “Just lie still, sweetheart. Let me take care of you.”

Sam’s not about to argue. His whole body aches, but in a pleasant way he knows he’ll be feeling in the morning, and he really just wants to sleep. He keeps his eyes on Y/N, though- watching as she unties each limb and rubs the marks left by the rope. She massages his arms before lowering them to his sides, preventing the muscles from cramping after being in one position for so long. When she disappears into the bathroom and returns with a wash cloth. She wipes him down gently.

“Feeling better?” she asks, wiping the sweat from his face and brushing his hair back.

“Mm-hmm.” He closes his eyes and leans into her touch.

“Don’t fall asleep on me yet, baby. I need you to drink some water first.”

Sam whines, but forces his eyes open. She brings a bottle of water from the hotel mini fridge and presses it to his lips. Once he starts drinking, he realizes how thirsty he is and downs most of the bottle in no time.

“Good,” she praises. “No, go use the bathroom and brush your teeth. I’ll be right here when you’re done. We can sleep after that.”

“Okay.”

His legs are unsteady, but she holds him up and helps him to the bathroom. Once he’s done in there, she tucks him back into the bed- the sheets are suddenly clean and he doesn’t bother to ask how- and curls against his side.

“I’m proud of you,” she whispers against his collarbone.

* * *

When morning comes, Sam can’t deny what he feels any longer. Not when her softness is nestled against his side, not with the lingering soreness from their activities the night before in his muscles. She’s got his heart all wrapped up in black eyes and black leather, and Dean is going to kill him when he finds out, so they’re just not going to tell him. Not yet, at least.

What he doesn’t know won’t hurt him, right?

* * *

Sam finds himself digging through the lore for everything he can find on souls being stolen to Hell. There’s not a lot of research done, and most of it indicates that they become demons the same as any other soul. This is good news. If Y/N is a demon like any other demon, then, if she chooses that option, the blood cure will work for her.

Sam isn’t sure how to bring it up to her, but she finds out on her own. Sam gave her one of his journals of notes to scour for something hopefully related to their current hunt, forgetting exactly what the contents of that journal are. They’re sitting together on the motel couch, her back against the far side and her bare toes tucked under his thigh. He has on hand on his book and one hand on her ankle, just resting there.

“Sam?”

“Hmmm?”

He looks up from his reading when she moves, shifting around to sit next to him on the couch. She has a finger marking her spot in her book and she opens it to that spot, letting it fall onto his thigh. She doesn’t have to point for him to know what she found.

“Is this true?” she asks, gazing up at him with a look he can’t read. “Can you… cure me?”

Her voice is soft, almost lost, almost hopeful, and it rips right into his heart as effectively as if she’d taken a knife to him.

“Yes,” he says, keeping his own voice just as soft. “I should’ve told you, but I didn’t know how to bring it up. I can cure you. If you want me to.”

She loops an arm around his neck, pulling him in and burying her face in his shoulder with a sharp sob. The books fall to the floor as he guides her to sit in his lap. She clings to him, fingers of one hand in his hair, fingers of the other digging into the back of his shoulder.

“Please,” she chokes out.

* * *

It’s not easy- far from it. She insists that Sam be the one to perform the ritual- he’s the only one she trusts to do it. Sam hates to cause her any harm, but Dean’s never done the ritual before. He did, however, donate his blood to the cause.

“Tie me down,” Y/N tells him when they arrive in the bunker dungeon. This is her first time in the bunker at all and this is her first experience with it, and that kills him. He wants her to feel at home here. Hopefully this experience doesn’t ruin her perspective of Sam’s home.

“Is that necessary?” he asks. “You’ll already be in the devil’s trap.”

“Yeah, but we don’t know how I’ll react. Better safe than sorry, right?”

“I guess.”

“Hey, hey, hey.” She pulls him to a halt, turning him to face her. “It’s gonna be okay, sweetheart. Everything will work out fine.”

“How do you know?”

She holds his face in her hands. “I trust you. Come one. Let’s make me human again.”

The process is long and hard. Cas comes in to help at one point, but for the most part Sam does the whole ritual on his own. It kills him when the spell causes Y/N pain. She encourages him to keep going, though, so he presses on. When he finishes the spell and she goes limp in the chair, his heart leaps into his throat.

“Y/N!” he gasps, falling to his knees beside her and quickly untying her wrists from the arms of the chair. He gathers her into his arms, suddenly aware of how small she is. “Y/N, please. Open your eyes.” He cradles his face in one hand. “Please.”

She’s breathing fine and he relaxes immediately at the sound. That’s good. He feels even better when her eyes flicker open, even though they’re still black. As he watches, the black fades away to reveal her sleepy gaze.

“Sam?” she murmurs.

“Hey, baby,” he says, making a noise somewhere between a sob and a laugh. “There you are.”

“Did it work?” she asks.

“It worked, Y/N. It worked.” Sam’s vision is blurry with the tears he’s fighting back.

She grabs his head and pulls him down into a kiss. “Thank you,” she sighs. “Thank you.”

“Sam? Everything okay down here?”

He wipes his eyes and twists to see Dean standing in the doorway, looking concerned.

“Yeah,” he says, getting up and helping Y/N stand as well. “Yeah, everything’s perfect.”

“It worked?” the older Winchester questions, glancing between the two of them. Sam has a feeling Dean saw more than he’s letting on.

Sam nods. “Yeah, it worked.”

Dean nods as well. “Good. I’m not okay with my brother dating a demon.”

Sam flushes and Y/N laughs. She curls one arm around Sam’s waist, tucking herself neatly against his side.

“You know, I really can’t blame you,” she says.

“I think this calls for some celebratory drinks,” Dean decides. “Let’s see if you can still drink me under the table.”

“Oh, you’re on.”

As Sam follows two of his three favorite people out of the dungeon, he can’t help feeling like everything is right in the world.


End file.
